


One Year Anniversary

by NEG85



Series: A Destiel Life [3]
Category: Supernatural
Genre: Alternate Universe, Alternate Universe - Human, Alternate Universe - Modern Setting, Anal Fingering, Anal Sex, Bisexual Dean Winchester, Bisexual Jessica Moore, Bisexual Male Character, Boys Kissing, Canon LGBTQ Male Character, Fluff and Smut, Gabriel/Sam Winchester Kissing, Gay Sex, Human Castiel (Supernatural), Human Gabriel (Supernatural), LGBTQ Character, LGBTQ Themes, M/M, Making Love, Pansexual Castiel (Supernatural), Pansexual Gabriel (Supernatural), Pansexual Sam Winchester, Polyamory
Language: English
Status: Completed
Published: 2021-01-09
Updated: 2021-01-09
Packaged: 2021-03-13 08:08:53
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 4,022
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28650312
Author URL: https://archiveofourown.org/users/NEG85/pseuds/NEG85
Summary: Dean has a question he wants to ask Cas, along with another surprise, for their one year anniversary.But first, they hang out with friends and meet someone new.
Relationships: Castiel & Gabriel (Supernatural), Castiel & Jessica Moore, Castiel & Sam Winchester, Castiel/Dean Winchester, Charlie Bradbury/Jessica Moore, Gabriel & Sam Winchester, Gabriel/Sam Winchester, Jessica Moore & Dean Winchester, Jessica Moore/Sam Winchester
Series: A Destiel Life [3]
Series URL: https://archiveofourown.org/series/2079090
Kudos: 20





	1. Chapter 1

**Author's Note:**

> I plan to come back and possibly edit more later, but wanted to go ahead and put this out for your enjoyment. :)

Cas and Dean decide to celebrate their 1yr anniversary by ordering in and having a movie marathon. 

But first, they agree to swing by for a game of cards at Dean’s younger brother, Sam’s apartment. 

Jessica, Sam’s girlfriend answers the door with a smile. “Hey guys.” She says, stepping back to let them in.

“You joining in this time, Jess?” Cas asks. 

“Yeah, Sam begged me and you know those puppy dog eyes he has. I just can’t tell him no when he pulls that.” 

Cas and Dean chuckle as they follow her into the living room.

“Hey guys!” Sam waves, with a controller in his hand. Sounds of gunshots ring loud from the screen as lights flash.

“C’mon, keep your eyes on the screen, man!” Gabe cries out.

Jessica sits beside Sam and his eyes move to her. “Have I told you how beautiful you are, yet today?” he asks, smiling ear to ear and kissing her.

She giggles against his lips.

The television screen flashes red.

Gabe drops to his knees dramatically, dropping his controller. “AND..we’re all dead now. THANKS, Sam.” he looks back to the kissing couple behind him. He sighs deeply and rolls his eyes.

Dean takes Cas’ hand and winks at him.

“Oh, geez! This is supposed to be a game night, not a makeout party!” Gabe protests, standing again and turning off the game system. “Can someone please grab the cards so we can decide what we want to play first?”

Sam sits up. “Alright, I’ll go grab my deck and you guys can fight over what we play.” he says, leaving the room.

Jessica sighs. “How about poker?”

“Jess, have you ever played against Dean?” Cas asks, warily.

“Hmph. Dean isn’t the one you should be worried about.” Gabe chimes in confidently.

“Hey babe, you wanna order a pizza or something?” Jess calls out. “You guys hungry? We could all go in on it together.” she adds, looking between Dean and Cas on the loveseat, and Gabe sitting on the floor.

“None for us, thanks.” Cas says with a glimmer in his eyes.

“We have plans for dinner later.” Dean adds, raising Cas’ hand to his lips and pressing a kiss against his knuckles.

“Ugh, okay we GET it. You’re smitten, you can stop flaunting it now.” Gabe groans.

“Jealous much?” Dean says, smugly.

“I think it’s sweet.” Jessica replies to Gabe. “I hope me and Sam are still like that when we’ve been together for a year.”

“We definitely will, sweetheart.” Sam adds, walking back into the room, holding the cards up.

“Finally!” Gabe says, scooting over to the coffee table. “So are we ordering pizza or what?” he asks.

“Sure, what kind?” Sam asks.

“Anything as long as there’s not pineapple or mushrooms.” Gabe answers, making a disgusted face.

“Alright, I’ll pull up the app and order it.” Sam says, looking down at his phone and typing.

“Well, Jess says she wants to play poker. What do you think, Sam? Gabe sounds pretty confident he’s gonna give us all a run for our money.” Dean says.

“What money?” Cas asks.

Everyone laughs.

“Well, Gabe’s never played against my girlfriend.” Sam smiles at Jessica.

“No offense, but your girlfriend hasn’t played against me.” Dean adds with a cocky grin.

“I’m totally up to watch her kick both your asses.” Sam chuckles.

“Oh come ON! You guys haven’t heard I’m the KING of poker?” Gabe questions, looking around to everyone.

Dean rolls his eyes, then kisses Cas on the cheek.

They all move to their places on the floor around the coffee table.

Well, I WOULD say we can play teams, but since I’m the odd man out, I guess that wouldn’t exactly be fair.”

*Knock*knock*Knock*

Everyone looks at Sam and Jessica.

“Whose that?” Sam asks, looking at Jessica.

She grins mischievously, silently getting up and answering the door.

Sam looks back to everyone and shrugs.

A tall red haired girl walks in behind Jessica. “This is my friend Charlie, Charlie this is everyone.” Jessica says, before taking her place beside Sam.

“I guess we have an even number now, so we can play teams.” Gabe says. “Come on over here by me, darlin’. You any good at poker?”

Charlie shyly holds her hand up to half-wave to everyone, then sits down beside Gabriel. “I love poker. I used to play with my ex girlfriend all the time.” She says. “I’m a lesbian, by the way.” she attempts to whisper to Gabe, but ends up speaking loud enough for everyone to still hear.

“Hey, no judgement here babe. Hot’s hot.” he waggles his eyebrows at her. 

Charlie laughs awkwardly. “Thanks, I guess.”

“Alright, are we gonna play some cards, or what?” Dean says. He looks over to Cas and winks.

“Sure, I’ll deal first.” Sam says, shuffling the cards.

“We betting with pennies again? And what about the winner? How about something actually worth playing for this time.” Gabe says.

“You sure talk big for someone just as broke as the rest of us.” Cas responds.

Gabe looks at Cas with a mocking gesture. “I just want to make it interesting.”

“What do you suggest then?” Dean asks.

“Hmmm. Well, how about the winning team kisses?” he says winking at Charlie.

“Deal. BUT with one condition.” Charlie answers.

Everyone looks at each other.

Gabe’s eyes are wide with a shocked expression.

“The condition IS, each person on the winning team gets to choose someone to kiss, AS LONG AS the person they choose agrees to it.”

“Fine, DEAL.” Gabe agrees, unenthusiastically.

Sam deals the cards around the table and everyone slides closer to their partners.

“Guess we all know who Gabe plans to try to kiss if they win.” Dean whispers to Cas.

He nods. “You think we can win?” Cas whispers back.

“Against these guys? Pfft. Of course.” Dean replies.

The game goes on and Dean and Cas are out first. “Dammit.” Dean says, as they lay their cards face down on the table. Cas whispers something in his ear and he grins and blushes.

Sam’s phone dings. “Pizza’s here!” he announces, getting up and heading out the door.

“So how long have you known these guys?” Gabe asks Charlie, pointing towards Jess.

“Well, I only met Sam a few weeks ago, but me and Jess go way back.”

“Really? Like did you two go to the same high school or something?” Gabe asks.

“Yeah actually.” Jess answers.

“Oh that’s cool. So you’ve been friends a long time then.” Dean says.

“Not really, we...used to be a lot closer.” Charlie says hesitantly.

“What changed? College? Just life?” Cas asks.

“Charlie and I used to date.” Jess says bluntly, causing Gabe to choke on his beer.

“Seriously?” he asks, still coughing.

“Yeah.” Charlie confirms, looking down at the floor.

After a few minutes, Sam comes back in with the pizza, the smell of garlic and pizza sauce fills the air.

Setting the box down on the corner of the table, Sam sits back beside Jess.

Charlie and Gabe lay down their cards first. “Full house.” Charlie says with a cocky grin.

Jess leans forward raising her eyebrows. “Royal Flush.” She answers confidently.

Sam sits back with an evil grin. “Told ya my girl’s a damn good poker player.”

“Okay, okay. We all know you two are just gonna kiss each other, so go ahead and get it over with.” Gabe says, with a sigh.

“Actually,” Jess says standing up and pointing at Charlie. “I choose you.”

Everyone looks at Charlie.

“I accept.” Charlie answers, without hesitation. She pushes off the table and stands up. She walks over to Jess and kisses her on the cheek.

“Aww, c’mon, REALLY?!” Gabe protests.

Both girls giggle. “Nobody said what KIND of kiss it was going to be.” Charlie adds.

“Sam, who do you pick?” Jess asks.

Sam looks around the room. “I choose Gabe.” Sam declares.

Cas and Dean look at each other and shrug.

Gabe’s jaw is on the floor, eyes wide. “Wh-Wait ME?! Seriously, you’re picking ME?!”

Sam shrugs. “Well, I’m not about to pick my brother OR his boyfriend.” he laughs. “But hey, if you want to pass, I can always,” he turns to face Jess.

“I accept!” Gabe shouts a little more excitedly than he means to, showing by the slight blush on his cheeks. “I mean, yeah sure...whatever. It’s cool.” he tries to smooth over his overeager outburst.

Sam walks over to Gabe. Gabe turns his head away with a sigh, waiting for the same type of kiss Charlie and Jess shared.

Sam almost doubles over to lean down far enough to meet Gabe’s face. He grabs his chin, turns his face back toward him and plants a firm kiss against his lips.

The kiss deepens, and Gabe grabs a handful of Sam’s ass.  
Dean looks away. “Well, that’s not something I ever wanna see again.”

Sam finally pulls away, leaving Gabe gasping for air. “DAMN!” he looks at Jess. “He kiss YOU like that?!” he asks.

Jess grins and raises her eyebrows, nodding.

Charlie smiles at Jess and blushes.

Dean clears his throat. “Well, it’s been fun guys but we got plans.”

Dean and Cas both get up from the floor.

“Aww, c’mon, don’t leave yet.” Gabe says.

“Sorry, Gabe. It’s our anniversary.” Cas replies, smiling at Dean taking his hand.


	2. Chapter 2

**Summary for the Chapter:**

> Here's the question...and some smut (with feelings)

Dean opens the door to his apartment and he and Cas walk in. “So, what do you think we should order, babe?” Dean asks, wrapping his arms around Cas from behind.

Cas hums happily at being in Dean’s arms before answering. “Uh, I don’t know. What did we get last? Was it chinese or Mexican?”

“It was Mexican, remember? The delivery guy forgot your side of rice and beans and our cheese dip.”

“Oh yeah. Their food is SO good.”

“It really is.” Dean agrees.

“Do you feel like chinese then?” Cas asks, attempting to look at Dean.

“Hmmm. Maybe. I don’t know. If we do, do you know what you want?”

Cas considers it. “Yeah, I guess so. Is that what you wanna do? You know, we could always just get burgers.”

Dean perks up. “Burgers for our anniversary?”

“I don’t mind. I know how much you love them, and it’s been a little while since we’ve had any. Would that make you happy, sweetheart?” Cas asks, grinning.

“Are you sure you’re okay with that? I don’t want you to just pick something because you know I want it. You gotta eat too, babe.” Dean says.

“I’m sure. You know what to get me right?” Cas asks.

Dean pulls away and turns Cas toward him, smiling. “Yeah, I know just what to get you.” he says, pressing a kiss to Cas’ forehead.

“Good, it’s settled then. I’ll go grab the dvds.” Cas says, heading to the living room.

Dean peeks around the corner to make sure Cas isn’t looking. He walks over to the fridge and reaches into the cabinet above it, pulling out a small black box. Slipping it in his jacket pocket, he picks up the phone and orders their food.

Cas puts in the first dvd, pausing it and sitting on the couch to wait for Dean.

Once off the phone, Dean joins Cas on the couch. “Hi.” he says, smiling.

“Hey, handsome.” Cas says, kissing him briefly. He presses play.

Dean puts his arm around Cas.

Cas settles against Dean as the previews start.

They are about 45 minutes into the first movie when they hear the buzz of the intercom. “I got it, babe.” Dean says, heading to the door.

Cas pauses the movie again and pulls out his phone, mindlessly scrolling through social media.

“Ready to eat?” Dean asks when he walks back in, grabbing some paper towels.

“Yep.” Cas answers, getting up and meeting Dean in the kitchen.

Dean cocks his head at Cas. “You don’t wanna eat in the living room?”

Cas wraps his arms around Dean’s neck.

Dean sets the food down on the counter and wraps his arms around Cas’ waist.

“I love you.” Cas says, looking up at Dean.

Dean chuckles. “I love you too, baby.” he responds. He sighs happily and kisses Cas. 

It’s a sweet kiss that deepens as Cas’ tongue presses against Dean’s lips. Cas presses him against the counter and Dean breaks the kiss. He makes an attempt to speak but Cas crashes their mouths back together.

Dean’s pulse begins to race. He presses Cas’ shoulders back from him a little. He tries to speak but once he sees the desire in Cas’ eyes, he quickly changes his mind. Picking Cas up, he pulls his legs around his waist. 

Cas kisses below Dean’s ear and down his neck, causing fire to spread through Dean’s veins. “I need you.” Cas whines.

“Where?” Dean barely breathes out the question as Cas semi-forcefully bites down on his shoulder.

“Table.” Cas gasps against Dean’s lips. He licks into his mouth eagerly, swallowing Dean’s moan.

Dean roughly pulls Cas’ thighs tighter against him, then lays him against the hard surface of the kitchen table. He’s careful to put his hand behind Cas’ head as he leans back.

Cas’ thighs still grip Dean’s hips.

Quickly unbuttoning Cas’ shirt, Dean kisses and licks down his neck and chest.

“I missed you last week.” Cas says.

“I know. I missed you too, sweetheart.” Dean answers, pulling off his jacket, followed by his own shirt off over his head.

Cas reaches up and undoes Dean’s belt, opens his zipper and pulls his jeans and boxers below his ass.

Dean seamlessly gets Cas’ jeans and boxers down, pulling them off completely and dropping them to the floor.

Cas spreads his legs and scoots to the edge of the table.

“Shit, where’d we have the lube last?” Dean asks, panting as he looks around.

Maybe left it in the bathroom? Or the end table drawer in the bedroom?” Cas guesses.

“Be right back.” Dean says, kissing Cas briefly then heading down the hallway.

Cas takes the opportunity to try to work himself loose a little as he waits. A single digit slides in with little resistance, though it’s a little too dry to be completely pain free. Still, he pants, pressing further in.

“Got it.” Dean says, as he dashes back into the room. Eyes dart to watch Cas finger himself. “Here.” he pours lube against Cas’ fingers.

“Mmmm.”

“That better, baby?”

“Yeah, much better.” Cas moans, adding two more fingers and continuing to stretch himself open.

“God you’re gorgeous, Cas.” Dean says, taking Cas’ length in his palm, stroking him.

“Fuck, Dean.” Cas breathes, eyes flutter closed.

“Does that feel good?” Dean asks, as his erection grows even harder. 

“Yes.” Cas answers, biting his lip. He moans.

“Cas.” Dean whimpers.

Cas opens his eyes, looking at Dean. “Please.” He pleads, removing his fingers.

Dean happily moves back between Cas’ legs, slicks himself with lube and gently pushes in, a little at a time. Watching Cas’ face for continued guidance just to make sure he’s not in pain or see if he needs him to stop.

“Oh, baby.” Cas moans as Dean’s head fully slips past his entrance.

“Still okay, honey?” Dean asks, stopping completely and taking Cas’ hand.

Cas nods. “Yeah, I’m okay. Just..keep going slow til you get all the way in.”

“Of course I will, babe. I promise I would never hurt you.”

“I know you wouldn’t, Dean.” Cas smiles, tears welling up.

Panic surges through Dean when he sees Cas’ face. “Am I hurting you?” he leans down, starting to slowly pull back.

“No!” Cas says, cupping Dean’s face. “That’s not..no, you’re not hurting me. Promise.” he says reassuring Dean.

“Then what’s wrong?” Dean’s eyes scanning Cas’ face nervously. Terrified he’s done something wrong, or he’s about to get bad news maybe.

Cas chuckles a little. “Nothing’s wrong. I just...I love you so much.” his tears spill out down his cheeks.

“Baby, I love you too.” Dean says, kissing Cas. “Please don’t cry.” He kisses him again. “Here, let’s move to the bed, okay? The table isn’t very romantic and I’m sure it can’t be too comfortable.”

“Okay.” Cas agrees, sniffling and wiping his face.

Dean pulls out slowly then picks him up bridal style and carries him to the bedroom. Pulling back the covers, he lays Cas against the bed, then climbs in beside him. He pulls Cas against his chest, cuddling as he pushes the rest of his clothes off. “I’m here baby, I got you.” he says, brushing his fingers through Cas’ hair.

Cas pulls away, looking at Dean again. Tears still falling. “Do you have any idea how wonderful you are, Dean?” he asks, barely brushing his fingertips across his lover’s chest. 

“WELL..” Dean starts with a sarcastic snarky reply.

“No, really. I’m serious.” Cas interrupts. 

His ocean eyes feel like they are looking straight into Dean’s soul. It’s always hard for him to take such straight compliments- or any, to be quite honest, but especially from Cas. And even more so when Cas is staring straight into his eyes. He finds himself looking away to escape from the raw emotions Cas evokes in him.

“Dean.” Cas lightly grasps Dean’s chin and tugs gently to urge him to look at him again. 

Dean resists.

“Please look at me, sweetheart.” Cas begs.

Dean bites his bottom lip and meets Cas’ gaze again.

“Please don’t hide from me.” Cas says, pressing his lips against Dean’s.

“Sorry.” Dean says, breaking the kiss but pressing his forehead against Cas’.

“You don’t have to be sorry. I just want you to know you’re safe. You never have to hide from me.”

Dean grins. “How do you do that?”

“Do what?” Cas asks, his eyebrows narrow.

“You’re just...so unbelievably amazing, Cas.” Dean presses their lips together again.

Cas pulls Dean back over him, spreading his legs once again. “I love you.” he says, tilting his hips up.

Crashing their lips together again, Dean scoots up between Cas’ thighs and presses in again. Slowly, the head of his cock slips inside.

“Don’t stop.” Cas pleads, fingers clinging to Dean’s shoulders.

Dean is being squeezed by Cas' incredible tightness. That paired with the insane heat his dick is throbbing, already dribbling pre-cum. Focusing on his breathing, he forces himself to hold back and not cum yet. ‘Too soon.’ he tells himself.

Cas moans as Dean bottoms out, fully and so deep in his ass. “Fuck.” Cas whimpers. “Move...please.” he cries breathlessly.

Starting to barely pull back and thrust back, softly, gently, he desperately wants to make sure he doesn’t hurt the man he loves.

Cas nods. “Faster. Harder.”

Still careful at first, Dean pulls back, then thrusts forward a little faster and harder than the first time. Then again a little faster and harder, still waiting for signs of pain from Cas.

Cas finally pulls his own hips up and away then pushes firmly back down, sliding Dean back into him fully.

At this Dean is convinced Cas is really okay and opened up enough to be comfortable and feel good now. He firmly grasps Cas’ hip with one hand, the other against his cheek. Kissing Cas deeply, passionately he moves with increasing speed and force of his thrusts.

Looking into Dean’s eyes, Cas moves his hands to Dean’s hips, pulling him against him.

“I love you, Cas.” Dean moans.

“I love you too.” Cas says. Suddenly he moans, throwing his head back in pleasure as Dean hits Cas prostate. “Uhhnnnn.”

“OH god, Cas.”

“Baby.”

They pant and cling to each other as they moan, both getting closer to the edge.

Cas begins stroking himself.

Dean knows they’re both right on the verge now. “Yeah, baby. Cum for me, Cas.”

“Ahhhh.” Cas moans, pumping his fist faster.

Thrusting faster, doing his best to match Cas’ rhythm he is sure to go as deep as he can and hitting as hard as he can against that glorious bundle of nerves inside Cas.

“Ahh….ohh...DEAN!” Cas whimpers just before he spills out over his hand and stomach.

“Fuck...Yeah...God...Cas...Oh, yeah” Dean groans as he tumbles over the edge too. Cock twitching, still inside, filling the condom. Slowly pulling out, Dean removes the condom carefully and gets up to throw it away. He comes back and lays down again beside Cas.

Cas rolls over, facing away from Dean and scoots back.

Dean squeezes his arm beneath Cas’ pillow and rests his other arm across Cas’ waist. His hand lazily caressing the soft skin of Cas’ stomach. He presses his forehead against Cas’ back and matches his breathing after a few deep breaths.

“Still wanna watch those movies?” Cas asks, yawning.

“Maybe after a nap.” Dean replies, eyes barely open. “You work tomorrow?” he asks.

“No, but I have class.”

Dean groans, “Ugh.”

Cas chuckles. “I know.”

“Early?”

“Not until 11.” Cas answers.

“M’kay.” Dean replies, eyes fluttering closed. He was JUST about to doze off when he remembered. ‘SHIT!’ “Babe?”

“Hmm.” Cas hummed lightly in response.

Dean sits up. “Babe?” he repeats, leaning over to look at Cas.

Cas’ eyes open groggily.

“I’m sorry baby, I know you’re sleepy. Can you..come here first though? Please?” Dean asks, reaching out for Cas’ hand.

Cas, takes Dean’s hand, letting him pull him to sit up. He licks his lips. “What’s up?” he asks.

“You still awake?” Dean asks, wanting to make sure he isn’t half asleep.

Cas nods. “Yeah, I’m awake.” his head lols to the side a little but his eyes stay open.

“You think I could ask you something? Or..would you rather me let you sleep first?”

Cas leans his head against Dean’s chest. “Did we eat? I’m hungry.” Cas says pulling back and looking up to Dean.

Dean laughs. “I completely forgot about the food.” he admits. Seemingly in response, his stomach growls.

“Let’s eat, let me wake up a little more and we can talk about whatever it was you wanted to ask me. Okay?” 

“Okay sweetheart.” Dean kisses Cas’ forehead and helps him up. They get dressed and go back to the kitchen. Cas sits at the table and Dean grabs the food and brings it over, sitting next to Cas.

Dean digs out Cas’ burger and slides it over along with his soda. He digs his own food out and they begin to eat.

After a few minutes Cas seems to be more alert. “What was it you wanted to talk about?” he asks.

“Oh. Yeah, I uh..” he thinks and remembers the box is still in his jacket. He reaches down on the floor and pulls it out of the pocket, setting it on the table in front of Cas.

Cas looks down at the simple little black box then back to Dean. “Wh-What is this?” he asks, seeming a little nervous.

“Go ahead, open it.” Dean grins, nodding toward the box.

Still looking unsure, Cas removes the lid and looks inside. “A key?” he asks, pulling it out and holding it in his hand. His eyebrows narrow as he looks at Dean. “To…your apartment?” he asks.

Dean is full on smiling now, eyes shining. “Actually, no. The key you’re holding is to a house. A house I just put a down payment on.”

“Wait, what?! You’re...You..Wait, but you said you wanted to ask me something?” Cas’ face is full of disbelief.

“Yep. I’m moving into my new house and...I was kinda hoping….you would want to move too. Like, live with me there.”

Cas’ eyes are wide and a shocked look on his face. “Are you...Are you serious?” Cas asks, searching Dean’s face.

“Of course I am.” Dean answers, taking Cas’ hand. “Will you move in with me? Into the new place?” he asks again more straight forward this time.

“Yes. Yes, I will.” Cas replies, leaning over and pulling Dean into a tight hug.

“I’m so glad you said yes.” Dean admits, grinning ear to ear with Cas in his arms.


End file.
